WO2012013754A1 - Nouveaux dérivés éthers de dioxime microbicides - Google Patents

Nouveaux dérivés éthers de dioxime microbicides Download PDF

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WO2012013754A1
WO2012013754A1 PCT/EP2011/063018 EP2011063018W WO2012013754A1 WO 2012013754 A1 WO2012013754 A1 WO 2012013754A1 EP 2011063018 W EP2011063018 W EP 2011063018W WO 2012013754 A1 WO2012013754 A1 WO 2012013754A1
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alkyl
halogen
alkoxy
compound
formula
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PCT/EP2011/063018
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Daniel Stierli
Kurt Nebel
Werner Zambach
Andrea Bortolato
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Syngenta Participations Ag
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Priority to US13/813,131 priority Critical patent/US20140162980A1/en
Priority to CA2804355A priority patent/CA2804355A1/fr
Priority to CN201180037088.9A priority patent/CN103038217A/zh
Priority to BR112013002073A priority patent/BR112013002073A2/pt
Priority to EP11736114.7A priority patent/EP2598487A1/fr
Priority to AU2011284714A priority patent/AU2011284714A1/en
Publication of WO2012013754A1 publication Critical patent/WO2012013754A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the present invention relates to novel microbiocidally active, in particular fungicidally active, cyclic bisoxime derivatives. It further relates to intermediates used in the preparation of these compounds, to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by
  • phytopathogenic microorganisms preferably fungi.
  • Fungicidally active bisoximes are described in WO08074418.
  • the present invention accordin ly relates to bisoxime derivatives of formula (I)
  • X represents X-2, X-3, X-4 or X-5:
  • alkylsulphinyl C1-C4 alkylsulphonyl, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, d- C 4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
  • R 1 and R 2 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl; each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyl, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyl group;
  • groupings X-2, X-3, X-4 and X-5 may contain at most one ring (i.e. a cycloalkyi group or halocycloalkyl group) which contains either only one of the radicals Z 1 to Z 14 or two radicals Z 1 to Z 14 or three radicals Z 1 to Z 14 or four radicals Z 1 to Z 14 as ring members; and wherein radicals Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 9 , Z 10 and Z 14 are not substituted by OH;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-Ce alkyl, Ci-C4-alkoxy-Ci-C 4 -alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10 , SH, d-C 8 alkylthio, C r C 8 alkylsulphinyl, C r C 8 alkylsulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR n COR 9 or
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R 12 ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d-C 4 haloalkyl, d-C 4 alkoxy
  • each R 10 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-d alkyl, d-d haloalkyl, d-d alkoxy, d-d haloalkoxy and Ci-d-alkoxy-Crd-alkyl; each R 11 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci -alkyl, C 3 -C 8 al
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups
  • halogen independently selected from halogen, CN, NH 2 , N0 2 , OH, Crd alkyl, d-d haloalkyi, d-d alkoxy and Crd haloalkoxy;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )-;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, O, N(R 14 ) or S;
  • each R 12 and R 13 independently of one another represent hydrogen, halogen, Crd alkyl, d-d haloalkyi, Crd alkoxy or Crd haloalkoxy;
  • R 14 represents hydrogen, OH, Crd alkyl, Crd alkoxy, C 3 -C 6 -cycloalkyl, d-C 8 alkylcarbonyl or d-C 8 haloalkylcarbonyl;
  • p and q are each independently 0, 1 or 2;
  • Halogen either as a lone substituent or in combination with another substituent (e.g. haloalkyi) is generally fluorine, chlorine, bromine or iodine, and usually fluorine, chlorine or bromine.
  • Each alkyl moiety (including the alkyl moiety of alkoxy, alkylthio, etc.) is a straight or branched chain and, depending on the number of carbon atoms it contains, is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, /so-propyl, sec-butyl, /so-butyl, te t-butyl, neo-pentyl, n-heptyl or 1,3-dimethylbutyl, and usually methyl or ethyl.
  • the alkenyl and alkynyl groups can be mono- or di-unsaturated and are examples thereof are derived from the above mentioned alkyl groups.
  • Haloalkyl moieties are alkyl moieties which are substituted by one or more of the same or different halogen atoms and are, for example, monofluoromethyl, difluoromethyl, thfluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2- difluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 1-fluoroethyl, 2-chloroethyl, pentafluoroethyl, l,l-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, and typically trichloromethyl, difluorochloromethyl, difluoromethyl, thfluoromethyl and
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, /so-propoxy, n-butoxy, /so-butoxy, sec-butoxy and tert-butoxy, and usually methoxy or ethoxy.
  • Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy, and usually difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio, /so-propylthio, n-butylthio, /so-butylthio, sec-butylthio or tert-butylthio, and usually methylthio or ethylthio.
  • Alkylsulphonyl is, for example, methylsulphonyl, ethyl sulphonyl, propyl sulphonyl, iso- propylsulphonyl, n-butylsulphonyl, /so-butylsulphonyl, sec-butylsulphonyl or tert- butylsulphonyl, and usually methylsulphonyl or ethylsulphonyl.
  • Alkylsulphinyl is, for example, methylsulphinyl, ethylsulphinyl, propylsulphinyl, iso- propylsulphinyl, n-butylsulphinyl, /so-butylsulphinyl, sec-butylsulphinyl or tert-butylsulphinyl, and usually methylsulphinyl or ethylsulphinyl
  • Cycloalkyl may be saturated or partially unsaturated, preferably fully saturated, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, /so-propoxymethyl or /so-propoxyethyl.
  • Aryl includes phenyl, naphthyl, anthracyl, fluorenyl and indanyl, but is usually phenyl.
  • Carbocycle includes cycloalkyl groups and aryl groups.
  • Heterocycloalkyl is a non-aromatic ring that may be saturated or partially unsaturated, preferably fully saturated, containing carbon atoms as ring members and at least one heteroatom selected from O, S and N as ring members.
  • Examples include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,4-dioxanyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, oxazinanyl, morpholinyl, thiomorpholinyl, imidazolidinyl, pyrazolidinyl and piperazinyl, preferably morpholinyl, pyrrolidinyl, piperdinyl and piperazinyl, more preferably morpholinyl and pyrollidinyl.
  • Heteroaryl is, for example, a monovalent monocyclic or bicyclic aromatic hydrocarbon radical.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazolyl.
  • bicyclic groups include quinolinyl, cinnolinyl, quinoxalinyl, benzimidazolyl, benzothiophenyl, and benzothiadiazolyl.
  • Monocyclic heteroaryl groups are preferred, preferably pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, pyridyl and imidazolyl being most preferred.
  • heterocycle and “heterocyclic ring” are used interchangeably and are defined to include heterocycloalkyl and heteroaryl groups. Any reference herein to a heterocycle or heterocyclic ring preferably refers to the specific examples given under the definition of heteroaryl and heterocycloalkyl above, and are preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl and imidazolyl.
  • a moiety is indicated as being (optionally) substituted, e.g. alkyl, this includes those moieties where they are part of a larger group, e.g. the alkyl in the alkylthio group, the alkyl in the alkoxy group etc..
  • a moiety is indicated as being optionally substituted by one or more other groups, preferably there are one to five optional substituents, more preferably one to three optional substituents.
  • X represents X-2, X-3, X-4 or X-5:
  • X represents X-3 or X-5. More preferably X represents X-3.
  • Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent methylene, halomethylene, CH(CH 3 ) or C(CH 3 ) 2 .
  • Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 13 and Z 14 represent methylene.
  • Each R 1 and R 2 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyl, C1-C4 alkylthio, C1-C4
  • Each R 3 and R 4 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl.
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl.
  • Each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyl, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups,
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyl group.
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci-d alkyl, Ci-d haloalkyl, C 3 -C 6 cycloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, d-d alkyl, d-d haloalkyl, d-d alkoxy and d-d haloalkoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyl group;
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, d-d alkyl, Crd haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group optionally substituted by halogen.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-Ce alkyl, d-d-alkoxy-Ci-d-alkyl, Ci-d-alkoxy-Ci-d-alkoxy-Ci-d-alkyl, C 3 -Ce cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10 , SH, d-C 8 - alkylthio, d-C 8 alkylsulphinyl, C r C 8 alkylsulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR n COR 9 or CR 9 N-
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and Ci-C 4 alkyl sulphonyl;
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , or Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C r C alkyl, C r C haloalkyl, C r C alkoxy and
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 , CN, N0 2 , Ci-Q alkyl, Ci-C 6 -alkoxy-Ci-C -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, OR 10 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or Ci-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C1-C4 alkyl,
  • each R 10 independently of one another represent hydrogen, Ci-C 4 alkyl, C 3 -C 6 cycloalkyi, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, benzyl, phen
  • each R 11 independently of one another represent hydrogen or d-C 8 alkyl, wherein the alkyl is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 , CN, N0 2 , d-C 6 alkyl, Ci-C -alkoxy-Ci-C -alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, Ci-C 4 -alkoxy, Ci-C 4 -alkenoxy, Ci-C 4 -alkynoxy, phenoxy, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or Ci-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, methyl and halomethyl;
  • each R 11 independently of one another represent hydrogen or Ci-C 8 alkyl, wherein the alkyl is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 , CN, N0 2 , d-C 6 alkyl, Ci-C -alkoxy-Ci-C -alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, Ci-C 4 -alkoxy, Ci-C 4 -alkenoxy, Ci-C 4 -alkynoxy, phenoxy, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or Ci-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, methyl and halomethyl;
  • each R 11 independently of one another represent hydrogen or Ci-C 8 alkyl, wherein the alkyl, is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 1 , Y 3 , Y 4 , and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 , CN, N0 2 , Ci-Ce alkyl, Ci-C -alkoxy-Ci-C -alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, d-C 4 -alkoxy, Ci-C 4 -alkenoxy, Ci-C 4 -alkynoxy, phenoxy, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or d-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen,
  • Y 2 and Y 5 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, or d- C haloalkyi;
  • halogen independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • each R 11 independently of one another represent hydrogen or Ci-Cs alkyl, wherein the alkyl is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 1 and Y 4 independently of one another represent d-C 8 alkyl, Ci-Cs alkoxy, C 3 -C 8 cycloalkyl, N(R n ) 2 , phenyl, pyridyl, pyrimidinyl, Ci-Cs alkylthio, Ci-Cs alkylsulphinyl, Ci-Cs alkylsulphonyl, wherein the alkyl, cycloalkyl, phenyl, pyrimidinyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , d-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and Ci-C 4 alkylsulphonyl.
  • Y 1 and Y 4 independently of one another represent Ci-C 4 alkyl, d-C 4 haloalkyi, OH, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, phenyl and pyridyl, wherein the phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and d-C 4 haloalkoxy.
  • Y 2 , Y 3 , Y 5 and Y 6 independently of one another represent hydrogen, CN, OR 10 , NH 2 , halogen, Ci-Cs alkyl, d-C 8 haloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl, SH, Ci-C 8 alkylthio, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy.
  • Y 2 , Y 3 , Y 5 , and Y 6 independently of one another represent hydrogen, CN, OH, NH 2 , halogen, d-C 4 alkyi, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, OH, CN, Ci-C 8 alkyi, Ci-C 8 haloalkyl, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, C 3 -C 8 cycloalkyl, phenyl, pyridyl, N(R n ) 2 or NR n COR 9 , wherein phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyi, d-C 4 haloalkyl, Ci-C 4 alkoxy and d- C 4 haloalkoxy.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, CN, OH, halogen, Ci-C 4 alkyi, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyi, d-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, CN, OH, NH 2 , halogen, d-C 4 alkyi, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, d-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy.
  • Y 2 , Y 3 , Y 5 , and Y 6 independently of one another represent hydrogen, Ci-C 4 alkyi, CN or Ci-C 4 alkoxy, wherein alkyi is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, Ci-C 4 alkyi, CN or Ci-C 4 alkoxy, wherein alkyi is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , or Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-d alkyl, Ci-C 4 haloalkyi, Ci-C
  • Y 1 and Y 2 , Y 4 and Y 5 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y 1 and Y 2 , Y 4 and Y 5 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-d alkyl, d-d haloalkyi, d-d alkoxy and d-d haloalkoxy.
  • Y 1 and Y 2 , Y 4 and Y 5 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring (e.g.
  • Y 2 and Y 5 independently of one another represent hydrogen, halogen, d-C 4 alkyl, or d-C 4 haloalkyi, preferably hydrogen, halogen, methyl or halomethyl, preferably hydrogen.
  • Each R 9 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d- C 4 haloalkyi, d-C 4 alkoxy and d-C 4 haloalkoxy.
  • each R 9 independently of one another represent Ci-C 8 alkyl or d-C 8
  • haloalkyi more preferably d-C 4 alkyl or d-C 4 haloalkyi.
  • Each R 10 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8
  • cycloalkyi C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl.
  • Each R 11 independently of one another represents hydrogen, OH, d-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, or COR 9 , wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen; wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different; wherein when two radicals R 11 are attached to the same nitrogen atom, both of these radicals cannot be OH, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy; and wherein when two radicals R 11 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8:
  • cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, Ci-C 4 -alkoxy and d-C 4 -haloalkoxy.
  • groups e.g. one to five groups, independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, Ci-C 4 -alkoxy and d-C 4 -haloalkoxy.
  • each R 11 independently of one another represent hydrogen, Ci-C 8 alkyl or COR 9 ; wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 11 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups independently selected from halogen, methyl and halomethyl.
  • each R 11 independently of one another represent hydrogen or d-C 4 alkyl; wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different; and wherein when two radicals R 11 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, methyl and halomethyl.
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 independently of one another represent -C(R 12 R 13 )-.
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene.
  • Each R 12 and R 13 independently of one another represent hydrogen, halogen, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • R 14 represents hydrogen, OH, CrC 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 -cycloalkyl, Ci-C 8
  • p and q are each independently of one another 0, 1 or 2.
  • p and q are each independently of one another 1 or 2.
  • X represents X-2, X-3, X-4 or X-5:
  • alkylsulphinyl Ci-C 4 alkylsulphonyl, phenyl or CN, wherein the phenyl is optionally
  • R 1 and R 2 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group;
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, d-C 4 alkyl or Ci-C 4 haloalkyl;
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Q-Q haloalkyl, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy and C r C 4 haloalkoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group;
  • radicals Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 9 , Z 10 and Z 14 are not substituted by OH;
  • Y 1 , Y 2 , ⁇ 3 , ⁇ 4 , ⁇ 5 and ⁇ 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-Ce alkyl, Ci-C -alkoxy-Ci-C -alkyl, Ci-C -alkoxy-Ci-C -alkoxy-Ci-C -alkyl, C 3 -C 8 cycloalky
  • each R 9 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 10 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 11 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, or COR 9 , wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups
  • halogen independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )-;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, O, N(R 14 ) or S;
  • R 14 represents hydrogen, OH, d-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 -cycloalkyl, Ci-C 8
  • alkylcarbonyl or Ci-C 8 haloalkylcarbonyl alkylcarbonyl or Ci-C 8 haloalkylcarbonyl
  • p and q are each independently 0, 1 or 2;
  • X represents X-3
  • Z 3 and Z 5 independently of one another represent methylene, halomethylene, CH(CH 3 ) or C(CH 3 ) 2 ;
  • R 3 and R 4 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl or d- C 4 haloalkyi;
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, C 3 -C 6 cycloalkyi, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, d- C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a Cs- Ce cycloalkyi group or a C 3 -C 6 halocycloalkyl group;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-Ce alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10 , SH, d-C 8 alkylthio, d-C 8 alkylsulphinyl, C r C 8 alkyl sulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR n C
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , or Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C r C 4 alkyl, d-C 4 haloalkyi, d-C 4 al
  • each R 9 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 10 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 11 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, or COR 9 , wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )-;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, O, N(R 14 ) or S;
  • each R 12 and R 13 independently of one another represent hydrogen, halogen, d-C 4 alkyl, d-d haloalkyl, Ci-C 4 alkoxy or d-C 4 haloalkoxy;
  • R 14 represents hydrogen, OH, Ci-C 4 alkyl, d-C 4 alkoxy, C 3 -C 6 cycloalkyi, Ci-C 8
  • X represents X-3
  • Z 3 and Z 5 independently of one another represent methylene, halomethylene, CH(CH 3 ) or C(CH 3 ) 2 ;
  • R 3 and R 4 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl or d- C 4 haloalkyl;
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, d-
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -
  • each R 9 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi,
  • each R 10 independently of one another represents hydrogen, d-C 8 alkyl, C 3 -C 8 cycloalkyi,
  • C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 11 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, or COR 9 , wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • Y 1 and Y 4 independently of one another represent Ci-C 8 alkyl, Ci-C 8 alkoxy, C 3 -C 8 cycloalkyi, N(R n ) 2 , phenyl, pyridyl, pyrimidinyl, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, wherein the alkyl, alkoxy, cycloalkyi, phenyl, pyrimidinyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C alkyl, d-C haloalkyl, d-C alkoxy, d-C haloalkoxy, d-C alkylthio, d-C alkylsulphinyl and Ci-C 4 alkylsulphonyl;
  • Y 2 , Y 3 , Y 5 , and Y 6 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10 , SH, Ci-C 8 alkylthio, d- C 8 alkylsulphinyl, C r C 8 alkylsulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR n COR 9 or CR 9 N-OR 10
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , or Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C alkyl, d-C haloalkyl, d-C alkoxy and
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene
  • Z 3 and Z 5 represent methylene
  • R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl;
  • R 5 and R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyl group optionally substituted by halogen;
  • each R 9 independently represents Ci-C 4 -alkyl or CrC 4 haloalkyl
  • each R 11 independently of one another represent hydrogen or d-C 4 alkyl
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 1 and Y 4 independently of one another represent Ci-C 4 alkyl, Ci-C 4 haloalkyl, OH, Ci-C 4 alkoxy, d-C 4 haloalkoxy, phenyl or pyridyl, wherein the phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C1-C4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy and C r C 4 haloalkoxy;
  • Y 2 , Y 3 , Y 5 , and Y 6 independently of one another represent hydrogen, CN, OH, NH 2 , halogen, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy;
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, methyl and halomethyl ⁇ 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene; p and q independently of one another represent 1 or 2.
  • Y 2 , Y 3 , Y 5 and Y 6 independently of one another represent hydrogen, CN, OR 10 , NH 2 , halogen, Ci-C 8 alkyl, d-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl, SH, Ci-C 8 alkylthio, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy; or independently Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbo
  • each R 9 independently of one another represents Ci-C 4 -alkyl or Ci-C 4 haloalkyl
  • each R 10 independently represents one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 - haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 11 independently of one another represent hydrogen or d-C 4 alkyl
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 2 , Y 3 , Y 5 , and Y 6 independently of one another represent hydrogen, CN, OH, NH 2 , halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy;
  • Y 1 and Y 2 , Y 4 and Y 5 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y 1 and Y 2 , or Y 4 and Y 5 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 9 independently represents Ci-C 4 -alkyl or Ci-C 4 haloalkyl
  • each R 11 independently of one another represent hydrogen or d-C 4 alkyl
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • X represents X-3
  • Z 3 and Z 5 represent methylene
  • R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 5 and R 6 together with the carbon atom they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • X represents X-3
  • Z 3 and Z 5 represent methylene
  • R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • R 5 and R 6 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R 5 and R 6 together with the carbon atom they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group.
  • Y 1 represents the same substituent as Y 4
  • Y 2 represents the same substituent as Y 5
  • Y 3 represents the same substituent as Y 6 .
  • Y 1 represents the same substituent as Y 4
  • Y 2 represents the same substituent as Y 5
  • Y 3 represents the same substituent as Y 6
  • p is the same as q and are either 1 or 2 (preferably 1)
  • G 1 represents the same substituent as G 4
  • G 2 represents the same substituent as G 5
  • G 3 represents the same substituent as G 6
  • Y 1 represents the same substituent as Y 4
  • Y 2 represents the same substituent as Y 5
  • Y 3 represents the same substituent as Y 6
  • p is the same as q and are either 1 or 2 (preferably 1)
  • G 1 represents the same substituent as G 4
  • G 2 represents the same substituent as G 5 and G 3 represents the same substituent as G 6
  • X is either X-3 or X-5 (preferably X-3) and wherein Z 3 represents the same substituent as Z 5 , Z 11
  • X represents X-3
  • Z 3 and Z 5 represent methylene
  • R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • R 5 R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, Ci-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyl group optionally substituted by halogen;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 CN, N0 2 , Ci-Cs alkyl, Ci-C 6 -alkoxy-Ci-C -alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, OR 10 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or d-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d- C
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C1-C4 alkyl, C1-C4 haloalkyl, C r C alkoxy and C r C haloalkoxy;
  • each R 10 independently of one another represent hydrogen, d-C 4 alkyl, C 3 -C 4 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 11 independently of one another represent hydrogen or d-C 8 alkyl, wherein the alkyl is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Z 3 and Z 5 represent methylene
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 5 R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a Cs- Ce cycloalkyi group optionally substituted by halogen;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 CN, N0 2 , Ci-Ce alkyl, Ci-Ci-alkoxy-Ci-Cralkyl, C 3 -C 6 cycloalkyi, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, d-Ci-alkoxy, Ci-C4-alkenoxy, Ci-C4-alkynoxy, phenoxy, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or d-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, methyl and halomethyl;
  • each R 11 independently of one another represent hydrogen or d-C 8 alkyl, , wherein the alkyl, is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene
  • Z 3 and Z 5 represent methylene;
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 5 R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyi or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 - C 6 cycloalkyl group optionally substituted by halogen;
  • Y 1 , Y 3 , Y 4 and Y 6 independently of one another represent hydrogen, halogen, N(R n ) 2 CN, Ci-C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, pyridyl, Ci-Ci-alkoxy, Q-Cr alkenoxy, Ci-Ci-alkynoxy, phenoxy, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl or Ci-C 8 alkylsulphonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, methyl and halomethyl;
  • Y 2 and Y 5 independently of one another represent hydrogen, halogen, methyl, halomethyl
  • each R 11 independently of one another represent hydrogen or d-C 8 alkyl, wherein the alkyl, is optionally substituted by one or more halogen;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene
  • the invention relates to compounds of the formula (IA)
  • Z 4 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are as defined for a compound of formula (I).
  • the preferred definitions of Z 4 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 defined in respect of compounds of formula (I) also apply to compounds of formula (IA).
  • Z 4 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are as defined for a compound of formula (I).
  • the preferred definitions of Z 4 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 defined in respect of compounds of formula (I) also apply to compounds of formula (IB).
  • the invention relates to compounds of the formula (IC)
  • Z 4 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are as defined for a compound of formula (I).
  • the preferred definitions of Z 4 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 defined in respect of compounds of formula (I) also apply to compounds of formula (IC).
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring then compounds with a ring formed by Y 1 and Y 2 and/or Y 4 and Y 5 together with the fragment of the pyridyl ring to which they are attached are preferred.
  • any of Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 can form a partially or fully unsaturated 5- to 7- membered carbocyclic ring or a 5- to 7-membered heterocyclic ring may be excluded, although it is preferred that these compounds are not excluded.
  • R represents -ONH 2 , halogen, -0-S0 2 -R , trichloroacetimidate, -ONH-CO-R 9 , -ONH-CO-OR 10 ;
  • R 16 represents d-d alkyl, d-d haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or two substituents independently selected from methyl, trihalomethyl, N0 2 , CN, Ci-C 7 alkoxycarbonyl;
  • At least one of Y 4 , Y 5 or Y 6 represents pyrimidinyl, d-C 8 haloalkylthio, Ci-C 8 haloalkylsulphinyl or d-C 8 haloalkylsulphonyl wherein the pyrimidinyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C alkyl, d-C haloalkyl, d-C alkoxy, d-C haloalkoxy, d- C 4 alkylthio, Ci-C 4 alkylsulphinyl and Ci-C 4 alkyl sulphonyl.
  • G 6 represents N(R 14 ) wherein R 14
  • R 15 represents -ONH 2 , -0-S0 2 -R 16 , trichloroacetimidate or halogen.
  • R 15 represents -ONH 2 , tosylate, mesylate, triflate or trichloroacetimidate.
  • the invention provides a compound of formula (III)
  • Z 5 , Z 8 , Z 9 , Z 12 , Z 13 and Z 14 are as defined for a compound of formula (I);
  • R 17 and R 18 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, d- C 4 haloalkyl, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4
  • G 4 , G 5 , G 6 , Y 4 , Y 5 , Y 6 and q are as defined for the compound of formula (I) described herein; or a salt or N-oxide thereof.
  • At least one of Y 4 , Y 5 or Y 6 represents pyrimidinyl, Ci-C 8 haloalkylthio, Ci-C 8 haloalkylsulphinyl or Ci-C 8 haloalkylsulphonyl ,wherein the pyrimidinyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C alkyl, C r C haloalkyl, C r C alkoxy, C r C haloalkoxy, C r C alkylthio, d-C 4 alkylsulphinyl and Ci-C 4 alkyl sulphonyl.
  • G 6 represents N(R 14 ) wherein R 14 represents C 3 -C 6 cycloalkyl.
  • R 17 and R 18 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.
  • X' represents X'-l.
  • the invention provides a compound of formula (IV) wherein G 4 , G 5 , G 6 , Y 4 , Y 5 , Y 6 and q are as defined for a compound of formula (I) providing that:
  • G 6 is -CH 2 - and Y 6 , Y 7 and Y 8 are H, then G 5 is not CH(CH 2 CH 3 );
  • Y 4 represents halogen, CN, N0 2 , Ci-C 8 alkyl, Ci-C 4 -alkoxy-Ci-Cralkyl, Ci-C 4 - alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10' , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR n COR 9 or CR 9 N-OR 10 , wherein the alkyl, cycloalkyi, alkenyl, alkyl, C
  • Y 4 represents Ci-C 8 alkyl, C 2 -C 8 alkoxy, C 3 -C 8 cycloalkyi, N(R n ) 2 , phenyl, pyridyl, pyrimidinyl, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, Ci-C 8
  • haloalkylthio Ci-C 8 haloalkylsulphinyl or d-C 8 haloalkyl sulphonyl, wherein the alkyl, cycloalkyi, phenyl, pyrimidinyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and Ci-C 4 alkylsulphonyl.
  • Y 4 represents Ci-C 4 alkyl, d-C 4 haloalkyl, OH, C 2 -C 4 alkoxy, C 2 -C 4 haloalkoxy, phenyl or pyridyl, wherein the phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d- C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • R 10' represents hydrogen, C 2 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 -alkyl, Ci-C -haloalkyl, Ci-C -alkoxy, Ci-C -haloalkoxy and Ci-C -alkoxy- Ci-C -alkyl.
  • At least one of Y 4 , Y 5 or Y 6 represents pyrimidinyl, Ci-C 8 haloalkylthio, Ci-C 8 haloalkylsulphinyl or Ci-C 8 ha loa I kyl sulphonyl, wherein the pyrimidinyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C r C alkyl, C r C haloalkyl, C r C alkoxy, C r C haloalkoxy, C r C alkylthio, d-C 4 alkylsulphinyl and Ci-C 4 a I kyl sulphonyl.
  • G 6 represents N(R 14 ) wherein R 14 represents C 3 -C 6 cycloalkyl or a salt or N-oxide thereof.
  • G 3 , G 5 , G 6 , Y 4 , Y 5 , Y 6 and q are as defined in respect of compounds of formula (I) above also apply to compounds of formula (IV).
  • the invention provides a process for the production of a compound of formula (I) comprising reacting a compound of formula (lib) with a compound of formula (V) as shown in scheme A
  • R represents halogen, -0-S0 2 -R or trichloroacetimidate
  • R 16 represents Ci-C 4 -alkyl, Ci-C 4 -haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or two substituents independently selected from methyl, trihalomethyl, N0 2 , CN, Ci-C 7 -alkoxycarbonyl; and
  • the invention relates to a process for the production of a compound of formula (I) comprising reacting a compound of formula (Via) with a compound of formula (Vila) to produce a compound of formula (Ila) and reacting the compound of formula (Ila) with a compound of formula (Villa) as shown in scheme B
  • X, G 1 , G 2 , G 3 , G 4 , G 5 , G 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , p, and q are as defined for the compound of formula (I) and wherein (Vila) is for example either used in its free form or in the presence of one or more acids, such as HCI, HBr, CH 3 COOH, oxalic acid, sulphuric acid, para-toluene-sulfonic acid.
  • a suitable amount of acid is e.g. a catalytic amount or it may be present up to 1 or 2 or more equivalents with respect to compound (Vila) .
  • the invention relates to a process for the production of a compound of formula (I) comprising reacting a compound of formula (Via) with a compound of formula (Villa) and a compound of formula (Vila) as shown in scheme C
  • X, G 1 , G 2 , G 3 , G 4 , G 5 , G 6 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , p, and q are as defined for the compound of formula (I) and wherein (Vila) is for example either used in its free form or in the presence of one or more acids, such as HCI, HBr, CH 3 COOH, oxalic acid, sulphuric acid, para-toluene-sulfonic acid.
  • a suitable amount of acid is e.g. a catalytic amount or it may be present up to 1 or 2 or more equivalents with respect to compound (Vila) .
  • the compounds of formula (I) may exist as different geometric or optical isomers or in different tautomeric forms. These may be separated and isolated by well-known (usually chromatographic) techniques, and all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms, such as deuterated compounds, are part of the present invention.
  • the carbon-nitrogen double bonds of the compound of formula (I) allow the four cis/trans isomers shown below:
  • the present invention includes each of these isomers.
  • the invention may provide a compound of formula (I) as just one of these isomers or as a mixture of one or more isomers in any ratio.
  • Preferred compounds are those of isomer (i).
  • the invention also includes the corresponding isomers of the intermediates described herein, e.g. compounds (II), (III) and (IV).
  • the scheme also includes synthesis of the other geometric isomers where possible.
  • Scheme A shown above encompasses the reactions below:
  • Table X represents Table 1 (when X is 1), Table 2 (when X is 2), Table 3 (when X is 3), Table 4 (when X is 4), Table 5 (when X is 5), Table 6 (when X is 6), Table 7 (when X is 7), Table 8 (when X is 8), Table 9 (when X is 9), Table 10 (when X is 10), Table 11 (when X is 11), Table 12 (when X is 12), Table 13 (when X is 13), Table 14 (when X is 14), Table 15 (when X is 15), Table 16 (when X is 16), Table 17 (when X is 17), Table 18 (when X is 18), Table 19 (when X is 19), Table 20 (when X is 20), Table 21 (when X is 21), Table 22 (when X is 22), Table 23 (when X is 23), Table 24 (when X is 24). Table X is 20 (when X is 20), Table 21 (when X is 21), Table 22 (when X is 22), Table 23 (when
  • Table 1 This table discloses compounds 1.001 to 1.692 of the formula (I-I)
  • Table 7 This table discloses compounds 7.001 to 7. 692 of the formula (I-VII)
  • Table 9 This table discloses compounds 9.001 to 9.692 of the formula (I-IX)
  • Table 10 This table discloses compounds 10.001 to 10. 692 of the formula (I-X)
  • Table 11 This table discloses compounds 11.001 to 11. 692 of the formula (I-XI)
  • Table 12 This table discloses compounds 12.001 to 12. 692 of the formula (I-XII)
  • Table 13 This table discloses compounds 13.001 to 13.692 of the formula (I-XIII)
  • Table 14 This table discloses compounds 14.001 to 14.692 of the formula (I-XIV)
  • Table 17 This table discloses compounds 17.001 to 17.692 of the formula (I-XVII)
  • Table 19 This table discloses compounds 19.001 to 19.692 of the formula (I-XIX)
  • Table 20 This table discloses com ounds 20.001 to 20.692 of the formula (I-XX)
  • Table 21 This table discloses compounds 21.001 to 21.692 of the formula (I-XXI)
  • Table 23 This table discloses compounds 23.001 to 23.692 of the formula (I-XXIII)
  • Table 24 This table discloses compounds 24.001 to 24.692 of the formula (I-XXIV)
  • the compounds in Tables 1 to 24 include all isomers, tautomers and mixtures thereof, including the cis/trans isomers shown above.
  • the compounds of the invention may be made by a variety of methods, illustrated in schemes 1-7.
  • the compounds depicted in the schemes also indicate any isomers and tautomers, in particular the geometric isomers arising from the oxime and oxime ether moieties.
  • Compounds of formula (I) may be prepared by reacting a compound of formula (Ila), wherein X, G 4 , G 5 , G 6 , q, Y 4 , Y 5 and Y 6 are as defined herein for compounds of formula (I), with a compound of formula (VIII), wherein G 1 , G 2 , G 3 , p, Y 1 , Y 2 and Y 3 are as defined herein for compounds of formula (I), and T 1 and T 2 are Ci-C 8 alkoxy, or T 1 and T 2 together with the carbon they are attached to form a carbonyl group or an acetal or ketal function of the form
  • Hydroxylamine derivatives of formula (Ila) may be made by reacting compounds of formula (VI), wherein G 4 , G 5 , G 6 , q, Y 4 , Y 5 and Y 6 are as defined herein for compounds of formula (I), and T 1 and T 2 are Ci-C 8 alkoxy, or T 1 and T 2 together with the carbon they are attached to form a carbonyl group or an acetal or ketal function of the form C(0-Ci-C 6 - alkylidene-O) whereby the alkylidene fragment may optionally be mono- to tetra-substituted by Ci-C 6 alkyl, with a bishydroxylamine derivative of formula (VII), wherein X is as defined herein for a compound of formula (I) and R 19 and R 20 are either hydrogen or suitable protecting groups such as tert-butyloxycarbonyl (BOC), allyloxycarbonyl,
  • fluorenylmethyloxycarbonyl (FMOC), formyl, acetyl, propionyl, trifluoroacetyl, benzoyl, substituted benzoyl, STABASE, Si(0-Ci-C 8 -alkyl) 3 , bis-Si(0-Ci-C 8 -alkyl) 3 , bis-benzyl, substituted bis-benzyl, bis-allyl, substituted bis-allyl, bis d-C 8 -alkoxy-alkyl, N- phenyl methylene, substituted N-phenylmethylene, trityl, benzhydryl, substituted benzhydryl, or R 19 and R 20 together with the nitrogen atom to which they are attached may form a phthalyl group (scheme 1).
  • General conditions for this type of condensation reaction can be found below.
  • R 19 and R 20 are hydrogen, in order to optimize the yield of compound (Ila) an excess of intermediate (V) over intermediate (IV) may preferably be used. If R 19 or R 20 is not hydrogen, the hydroxylamine derivative may be deprotected using techniques well known to the person skilled in the art. Examples can be found in Greene, T. W., Wuts, P. G. N., Protective Groups in Organic Synthesis, John Wiley & Sons, Inc, 2006.
  • compounds of formula (I) may be prepared by reacting a compound of formula (IV) and a compound of formula (VIII) in the presence of a compound of formula (Vila), that is a compound of formula (VII) wherein R 19 and R 20 are both hydrogen.
  • a compound of formula (Vila) that is a compound of formula (VII) wherein R 19 and R 20 are both hydrogen.
  • compounds of formula (I) can be obtained by reacting a compound of formula (lib), that is a compound of formula (II) wherein R is a halogen, in particular chlorine, bromine or iodine, or a sulfonic acid ester group, such as mesylate, tosylate, triflate, a phenylsulfonic acid ester, a nitro-phenylsulfonic acid ester, or a
  • Compounds of formula (lib) may be obtained by reacting an oxime of formula (IV) wherein G 4 , G 5 , G 6 , q, Y 4 , Y 5 and Y 6 are as defined herein for compounds of formula (I), with a compound of formula (X), wherein R 15 is as defined herein for compounds of formula (lib) and R 21 is a halogen, in particular chlorine, bromine or iodine, a sulfonic acid ester group, or trichloroacetimidate (scheme 3).
  • R 15 and R 21 may be the same or different.
  • R 21 is a better leaving group under the conditions of the reaction, such as tosylate or 5 bromine when R 15 is chlorine.
  • an excess of the compound of formula (X) relative to the oxime (IV) would be used in the reaction, especially when R 15 and R 21 are the same.
  • Oximes of formula (IV) may be obtained by a condensation reaction, whereby a compound of formula (VI), wherein G 4 , G 5 , G 6 , q, Y 4 , Y 5 and Y 6 are as defined herein for compounds of formula (I) and T 1 and T 2 are Ci-C 8 alkoxy, or T 1 and T 2 together with the
  • oximes of formula (IV) can be obtained by a nitrosation reaction of compounds of formula (XIV), wherein G 4 , G 5 , G 6 , q, Y 4 , Y 5 and Y 6 are as defined herein for compounds of formula (I), with base and an alkyl nitrite, as seen in scheme 5.
  • Typical bases include lithium diisopropyl amide (LDA), lithium hexamethyldisilazane, n-butyl lithium, s-butyl lithium, tert-butyl lithium, sodium tert-butylate or potassium tert-butylate .
  • Typical alkyl nitrites include isopentyl nitrite and tert-butyl nitrite.
  • the compound of formula (XIV), the alkyl nitrite or the base can be used in different stoichiometric amounts, with each reagent possibly being in excess with respect to the others.
  • such reactions are carried out under non-aqueous conditions in an inert solvent such as hexane, heptanes, cyclohexane, toluene or ethers such as THF or tert-butyl methyl ether.
  • the reaction may be performed at temperatures ranging from -80 to 250°C, preferably between -50 and 120°C. Similar conditions can be used to prepare oximes of formula (X).
  • Such reactions can lead to a mixture of the E- and the Z-oxime (ether) product, or the product may also be exclusively either the E- or the Z-oxime (ether).
  • the compounds of (lib) can be formed by reacting a hydroxylamine derivative of formula (XII), wherein R 15 is halogen, with a compound of formula (VI), as seen in scheme 6.
  • a compound of formula (VI) as seen in scheme 6.
  • Compounds of formula (XII) can be made by alkylating a hydroxylamine derivative of formula (XI), wherein R 22 and R 23 , either independently of each other, or together with each other and the nitrogen atom to which they are attached, are protecting groups, such as tert-butoxy carbonyl, acetyl, benzyl, or phthalyl, with the alkylating agent (X), wherein R 15 is halogen and R 21 is halogen, in particular chloro, bromo or iodo, a sulfonic acid ester group, or trichloroacetimidate (scheme 6). Typical conditions for such an alkylation reaction may be found below.
  • the protecting groups or group can then be removed using techniques well known to a person skilled in the art, examples of which can be found in Greene, T. W., Wuts, P. G. N., Protective Groups in Organic Synthesis, John Wiley & Sons, Inc, 2006.
  • Z 5 , Z 8 , Z 9 , Z 12 , Z 13 and Z 14 are as defined herein for compounds of formula (I), and R 17 and R 18 independently of one another represent hydrogen, halogen, d-C 4 alkyl, Q- C 4 haloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g.
  • one to five groups can be made by reacting compounds of formula (III), wherein G 4 , G 5 , G 6 , Y 4 , Y 5 , Y 6 and q are as defined herein for formula (I) and R 17 and R 18 independently of one another represent hydrogen, halogen, Ci-Q alkyl, Q-Q haloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, d-d alkyl, Crd haloalkyl, d-d alkoxy and Crd haloalkoxy, with compounds of formula (V) which have been described herein.
  • the reaction may be performed in the presence or absence of an inert organic or inorganic solvent, or in the presence of a mixture of such solvents. Preferentially, it is performed in the presence of one or more solvents.
  • Preferred solvents include the following aliphatic or aromatic hydrocarbons, which may optionally be substituted by one or more halogen atoms, such as pentane, hexanes, heptanes, cyclohexane, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzenes, dichloromethane, chloroform, 1,2-dichloroethane or carbon tetrachloride, ethers such as diethylether, diisopropyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane or diglycol dimethyl ether, ketones such as acetone
  • solvents includes water and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • the reaction may be performed between -20 C and 250 C, preferentially between 0 ° C and lOO C. In some cases the reaction mixture may be heated to reflux.
  • compounds can be used in the form of the free compound, or, alternatively, they can be used in the form of a salt such as the acetate, trifluoroacetate, propionate, benzoate, oxalate, methyl solfonate, phenylsulfonate, p-tolylsulfonate, trifluormethylsulfonate, fluoride, chloride, bromide, iodide, sulphate, hydrogensulphate or nitrate, including bis-salts if appropriate.
  • a salt such as the acetate, trifluoroacetate, propionate, benzoate, oxalate, methyl solfonate, phenylsulfonate, p-tolylsulfonate, trifluormethylsulfonate, fluoride, chloride, bromide, iodide, sulphate, hydrogensulphate or nitrate, including bis-salts if appropriate.
  • the reaction can be carried out in the absence of an acid using the free compounds. Alternatively, the reaction may be performed in the presence of an acid in catalytic, stoichiometric or excess amounts. Acids that could be used include acetic acid, propionic acid, oxalic acid, trifluoroacetic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, methansulfonic acid, para-toluenesulfonic acid, sulphuric acid, sodium hydrogensulphate and phosphoric acid.
  • the reaction can optionally be carried out in a water-free solvent system in the presence of a drying agent, such as sodium or magnesium sulphate, potassium carbonate or molecular sieves.
  • the condensation reaction can lead to a mixture of the E- and the Z-oxime (ether) product.
  • the condensation product may also be exclusively either the E- or the Z- oxime (ether).
  • Condensations can be performed under reduced pressure, normal pressure or increased pressure. Preferentially the reaction is performed under normal pressure.
  • the reaction may be performed in the absence or presence of a solvent or a mixture of solvents.
  • Preferential solvents include the following aliphatic or aromatic hydrocarbons that may optionally be substituted by one or more halogen atoms such as pentane, hexanes, heptanes, cyclohexane, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzenes, dichloromethane, chloroform, 1,2-dichloroethanev or carbon tetrachloride, ethers such as diethyl ether, diisopropyl ether, tert-butyl-methyl ether, tetrahydrofuran, 1,4- dioxane, dimethoxyethane or diglycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl
  • the selction of solvents includes also water and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • the reaction may be performed in a biphasic system comprising an organic solvent that is not miscible with water, such as toluene, dichloromethane, dichloro-ethylene, and an aqueous solvent, such as water.
  • a phase-transfer catalyst such as tetra-n-butylammonium bromide (TBAB)
  • TDMBAC Tetradecyldimethylbenzylammonium chloride
  • N-Benzyltrimethylammonium hydroxide N-Benzyltrimethylammonium hydroxide
  • the biphasic reaction may be performed with or without ultrasonication.
  • the reaction may be carried out at temperatures varying from -100°C and 250°C.
  • the temperature range is between 0°C and 100°C.
  • an organic or inorganic base may be present such as alkali- and earth alkali acetates, amides, carbonates, hydrogencarbonates, hydrides, hydroxides or alcoholates such as sodium, potassium, caesium or calcium acetate, sodium, potassium, caesium or calcium carbonate, sodium, potassium, caesium or calcium hydrogencarbonate, sodium, potassium, caesium or calcium hydride, sodium, potassium, caesium or calcium amide, sodium, potassium, caesium or calcium hydroxide, sodium, potassium, caesium or calcium
  • methanolate sodium, potassium, caesium or calcium ethanolate, sodium, potassium, caesium or calcium n-, i-, s- or t-butanolate, triethylamine, tri propylamine, tributylamine, di- isopropyl-ethylamine, ⁇ , ⁇ -dimethyl-cyclohexylamine, N-methyl-dicyclohexylamine, N,N- dimethyl-aniline, N,N-diethyl-aniline, ⁇ , ⁇ -dimethyl-benzylamine, N,N-diethyl-benzylamine, pyridine, 2-methyl-pyridine, 3-methyl-pyridine, 4-methyl-pyridine, 2,6-dimethyl-pyridine, 2,4,6-trimethyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl-piperidine, N-methyl-morpholine, N-ethyl-morpholine, N
  • the alkylation can be performed under reduced pressure, normal pressure or increased pressure. Preferentially the reaction is performed under normal pressure.
  • steps 1) to 12) may be required to be purified using, for example, chromatography, crystallisation or other purification techniques well known to the person skilled in the art.
  • the compounds of formula (I) to formula (XIII) and, where appropriate, the tautomers thereof, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • the invention therefore also relates to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a compound of formula (I) is applied as active ingredient to the plants, to parts thereof or the locus thereof.
  • the compounds of formula (I) according to the invention are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous useful plants.
  • the compounds of formula (I) can be used to inhibit or destroy the diseases that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • compounds of formula (I) as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the compounds of formula (I) according to the invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage or in hygiene management.
  • the compounds of formula (I) are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara).
  • Fungi imperfecti e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria
  • Basidiomycetes e.g. Rhizoctonia, Hemileia, Puccinia
  • useful plants to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco
  • useful plants is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield ® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady ® , Herculex I ® and LibertyLink ® .
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • YieldGard ® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm ® (maize variety that expresses a CrylllB(bl) toxin); YieldGard Plus ® (maize variety that expresses a CrylA(b) and a CrylllB(bl) toxin); Starlink ® (maize variety that expresses a Cry9(c) toxin); Herculex I ® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B ® (cotton variety that expresses a CrylA(c) toxin); Bollgard I ® (cotton variety that expresses a CrylA(c) toxin); Bollgard II
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • locus of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil.
  • An example for such a locus is a field, on which crop plants are growing.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material” is understood to denote seeds.
  • the compounds of formula (I) can be used in unmodified form or, preferably, together with carriers and adjuvants conventionally employed in the art of formulation.
  • the invention also relates to compositions for controlling and protecting against phytopathogenic microorganisms, comprising a compound of formula (I) and an inert carrier, and to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a composition, comprising a compound of formula (I) as active ingredient and an inert carrier, is applied to the plants, to parts thereof or the locus thereof.
  • compounds of formula (I) and inert carriers are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances.
  • the methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
  • the compounds of formula (I) or compositions, comprising a compound of formula (I) as active ingredient and an inert carrier can be applied to the locus of the plant or plant to be treated, simultaneously or in succession with further compounds.
  • further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • a preferred method of applying a compound of formula (I), or a composition, comprising a compound of formula (I) as active ingredient and an inert carrier is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen.
  • the compounds of formula (I) may also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation i.e. a composition comprising the compound of formula (I) and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
  • the agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula (I), 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from lOg to 1kg a.i./ha, most preferably from 20g to
  • 600g a.i./ha When used as seed drenching agent, convenient rates of application are from lOmg to lg of active substance per kg of seeds.
  • the rate of application for the desired action can be determined by experiments. It depends for example on the type of action, the developmental stage of the useful plant, and on the application (location, timing, application method) and can, owing to these parameters, vary within wide limits.
  • the compounds of formula (I), or a pharmaceutical salt thereof, described above may also have an advantageous spectrum of activity for the treatment and/or prevention of microbial infection in an animal.
  • Animal can be any animal, for example, insect, mammal, reptile, fish, amphibian, preferably mammal, most preferably human.
  • Treatment means the use on an animal which has microbial infection in order to reduce or slow or stop the increase or spread of the infection, or to reduce the infection or to cure the infection.
  • Prevention means the use on an animal which has no apparent signs of microbial infection in order to prevent any future infection, or to reduce or slow the increase or spread of any future infection.
  • a compound of formula (I) in the manufacture of a medicament for use in the treatment and/or prevention of microbial infection in an animal.
  • a compound of formula (I) as a pharmaceutical agent.
  • a compound of formula (I) as an antimicrobial agent in the treatment of an animal.
  • a pharmaceutical composition comprising as an active ingredient a compound of formula (I), or a pharmaceutically acceptable salt thereof, and a
  • This composition can be used for the treatment and/or prevention of antimicrobial infection in an animal.
  • This pharmaceutical composition can be in a form suitable for oral administration, such as tablet, lozenges, hard capsules, aqueous suspensions, oily suspensions, emulsions dispersible powders, dispersible granules, syrups and elixirs.
  • this pharmaceutical composition can be in a form suitable for topical application, such as a spray, a cream or lotion.
  • this pharmaceutical composition can be in a form suitable for parenteral administration, for example injection.
  • this pharmaceutical composition can be in inhalable form, such as an aerosol spray.
  • the compounds of formula (I) may be effective against various microbial species able to cause a microbial infection in an animal.
  • microbial species are those causing Aspergillosis such as Aspergillus fumigatus, A. flavus, A. terms, A. nidulans and A. niger, those causing Blastomycosis such as Blastomyces dermatitidis; those causing
  • Candidiasis such as Candida albicans, C. glabrata, C. tropicalis, C. parapsilosis, C. krusei and C. lusitaniae; those causing Coccidioidomycosis such as Coccidioides immitis; those causing Cryptococcosis such as Cryptococcus neoformans; those causing Histoplasmosis such as Histoplasma capsulatum and those causing Zygomycosis such as Absidia corymbifera, Rhizomucor pusillus and Rhizopus arrhizus.
  • Fusarium Spp such as Fusarium oxysporum and Fusarium solani
  • Scedosporium Spp such as Scedosporium apiospermum and Scedosporium prolificans.
  • Microsporum Spp Trichophyton Spp, Epidermophyton Spp, Mucor Spp, Sporothorix Spp, Phialophora Spp, Cladosporium Spp, Petriellidium spp, Paracoccidioides Spp and Histoplasma Spp.
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the present invention provides a fungicidal composition
  • a fungicidal composition comprising a fungicidally effective amount of a compound of formula (I), optionally comprising an additional active ingredient.
  • the compound of formula (I) may be the sole active ingredient of the
  • composition or it may be admixed with one or more additional active ingredients such as an insecticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • additional active ingredients such as an insecticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • additional active ingredients such as an insecticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • additional active ingredients such as an insecticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • additional active ingredients such as an insecticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • biocidally active ingredient are known for example from "The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition (New edition (02 Nov 2003)); Editor: C. D. S. Tomlin; The British Crop Protection Council, ISBN-10: 1901396134; ISBN-13: 978-1901396133] or its electronic version "e-Pesticide Manual V4.2" or
  • TX means a compound encompassed by the compounds of formula I, or preferably the term “TX” refers to a compound selected from the Tables 1-24):
  • oxytetracycline + TX paclobutrazole + TX, paraffin oil + TX, paraformaldehyde + TX, pencycuron + TX, pentachloronitrobenzene + TX, pentachlorophenol + TX, penthiopyrad + TX, perfurazoate + TX, phosphoric acid + TX, polyoxin + TX, polyoxin D zinc salt + TX, potassium bicarbonate + TX, probenazole + TX, procymidone + TX, propamocarb + TX, propineb + TX, proquinazid + TX, prothiocarb + TX, pyrazophos + TX, pyrifenox + TX, pyroquilon + TX, quinoxyfen + TX, quintozene + TX, silthiofam + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, strepto
  • X is a bivalent group selected from
  • Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R 2 is bromine, R 3 is methyl, R 4 is CN and X is Xi;
  • Ri is methyl substituted by cyclopropyl, R 2 is CF 3 , R 3 is methyl, R 4 is CI and X is Xi; c) Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R 2 is CF 3 , R 3 is methyl, R 4 is CI and X is Xi;
  • Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R 2 is CF 3 , R 3 is methyl, R is CN and X is Xi;
  • Ri is cyclopropyl substituted by cyclopropyl at the 1-position, R 2 is OCH 2 CF 3 , R 3 is methyl, R 4 is CN and X is Xi;
  • Ri is isopropyl, R 2 is methoxy; R 3 is methyl, R 4 is hydrogen and X is X 8 ;
  • Ri is isopropyl, R 2 is trifluoromethyl, R 3 is chlorine, R 4 is hydrogen and X is Xs;
  • Ri is isopropyl, R 2 is trifluoromethyl, R 3 is methyl, R 4 is hydrogen and X is X 8 ;
  • Ri is methyl, R 2 is bromine, R 3 is methyl, R 4 is CN and X is Xi ;
  • Ri is methyl
  • R 2 is bromine
  • R 3 is methyl
  • R 4 is CI
  • X is Xi
  • compositions comprising a compound of formula TX and
  • a strobilurin fungicide + TX (B2) an azole fungicide + TX, (B3) a morpholine fungicide + TX, (B4) an anilinopyrimidine fungicide + TX, (B5) a fungicide selected from the group consisting of
  • a strobilurin fungicide selected from azoxystrobin (47) + TX, dimoxystrobin (226) + TX, fluoxastrobin (382) + TX, kresoxim-methyl (485) + TX, metominostrobin (551) + TX, orysastrobin + TX, picoxystrobin (647) + TX, pyraclostrobin (690); trifloxystrobin (832) + TX, a compound of formula B-1.1 +TX
  • an azole fungicide selected from azaconazole (40) + TX, bromuconazole (96) + TX, cyproconazole (207) + TX, difenoconazole (247) + TX, diniconazole (267) + TX,
  • a morpholine fungicide mixture selected from aldimorph + TX, dodemorph (288) + TX, fenpropimorph (344) + TX, tridemorph (830) + TX, fenpropidin (343) + TX, spiroxamine (740) + TX, piperalin (648) and a compound of formula B-3.1 +TX
  • an anilino-pyrimidine fungicide selected from cyprodinil (208) + TX, mepanipyrim (508) and pyrimethanil (705);
  • a fungicide mixture selected from the group consisting of
  • a plant-bioregulator selected from the group consisting of
  • an insecticide selected from the group consisting of
  • a strobilurin fungicide selected from the group consisting of azoxystrobin + TX, dimoxystrobin + TX, fluoxastrobin + TX, kresoxim-methyl + TX, metominostrobin + TX, orysastrobin + TX, picoxystrobin + TX, pyraclostrobin; trifloxystrobin and a compound of formula B-l.l;
  • an azole fungicide selected from the group consisting of azaconazole + TX,
  • an anilino-pyrimidine fungicide selected from the group consisting of cyprodinil + TX, mepanipyrim and pyrimethanil;
  • a fungicide selected from the group consisting of benalaxyl + TX, benalaxyl-M + TX, benomyl + TX, bitertanol + TX, boscalid + TX, captan + TX, carboxin + TX, carpropamid + TX, chlorothalonil + TX, copper + TX, cyazofamid + TX, cymoxanil + TX, diethofencarb + TX, dithianon + TX, famoxadone + TX, fenamidone + TX, fenhexamide + TX, fenoxycarb + TX, fenpiclonil + TX, fluazinam + TX, fludioxonil + TX, flutolanil + TX, folpet + TX, guazatine + TX, hymexazole + TX, iprodione + TX
  • a plant-bioregulator selected from acibenzolar-S-methyl + TX, chlormequat chloride + TX, ethephon + TX, mepiquat chloride and trinexapc-ethyl;
  • an insecticide selected from abamectin + TX, emamectin benzoate + TX, tefluthrin + TX, thiamethoxam + TX, and glyphosate + TX, a compound of formula V
  • component (B) in combination with component TX surprisingly and substantially may enhance the effectiveness of the latter against fungi, and vice versa. Additionally, the method of the invention is effective against a wider spectrum of such fungi that can be combated with the active ingredients of this method, when used solely.
  • the active ingredient mixture of component TX to component (B) comprises compounds of formula I and a further, other biocidally active ingredients or compositions or if desired, a solid or liquid adjuvant preferably in a mixing ratio of from 100: 1 to 1:6000, especially from 50: 1 to 1:50, more especially in a ratio of from 20: 1 to 1:20, even more especially from 10: 1 to 1: 10, very especially from 5: 1 and 1:5, special preference being given to a ratio of from 2: 1 to 1:2, and a ratio of from 4: 1 to 2: 1 being likewise preferred, above all in a ratio of 1: 1, or 5: 1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3: 1, or 3:2, or 2: 1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1: 150, or 1:35, or 2
  • a further aspect of the invention are compositions, wherein component TX and component (B) are present in the composition in amounts producing a synergistic effect.
  • This synergistic activity is apparent from the fact that the fungicidal activity of the composition comprising component TX and component (B) is greater than the sum of the fungicidal activities of component TX and of component (B).
  • This synergistic activity extends the range of action of component TX and component (B) in two ways.
  • synergism corresponds to a positive value for the difference of (O-E).
  • expected activity said difference (O-E) is zero.
  • a negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
  • compositions according to the invention can also have further surprising advantageous properties.
  • advantageous properties are: more advantageuos degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination.
  • compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides.
  • compositions according to the invention it is possible to inhibit or destroy the phytopathogenic microorganisms which occur in plants or in parts of plants (fruit, blossoms, leaves, stems, tubers, roots) in different useful plants, while at the same time the parts of plants which grow later are also protected from attack by phytopathogenic microorganisms.
  • compositions according to the invention can be applied to the phytopathogenic microorganisms, the useful plants, the locus thereof, the propagation material thereof, storage goods or technical materials threatened by microorganism attack.
  • the compositions according to the invention may be applied before or after infection of the useful plants, the propagation material thereof, storage goods or technical materials by the microorganisms.
  • a further aspect of the present invention is a method of controlling diseases on useful plants or on propagation material thereof caused by phytopathogens, which comprises applying to the useful plants, the locus thereof or propagation material thereof a composition according to the invention.
  • a method which comprises applying to the useful plants or to the locus thereof a composition according to the invention, more preferably to the useful plants.
  • a method which comprises applying to the
  • the components (B) are known. Where the components (B) are included in "The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular component (B); for example, the compound "abamectin” is described under entry number (1). Most of the components (B) are referred to hereinabove by a so-called “common name”, the relevant "ISO common name” or another "common name” being used in individual cases. If the designation is not a "common name”, the nature of the designation used instead is given in round brackets for the particular component (B); in that case, the IUPAC name, the
  • benthiavalicarb (CAS 413615-35-7); cadmium chloride (CAS 10108-64-2); cedar leaf oil (CAS 8007-20-3); chlorine (CAS 7782-50-5); cinnamaldehyde (CAS: 104-55-2); copper
  • ammoniumcarbonate (CAS 33113-08-5); copper oleate (CAS 1120-44-1); iodocarb (3-Iodo- 2-propynyl butyl carbamate) (CAS 55406-53-6); hymexazole (CAS 10004-44-1); manganous dimethyldithiocarbamate (CAS 15339-36-3); mercury (CAS 7487-94-7; 21908-53-2; 7546-30- 7); metrafenone (CAS 220899-03-6); neem oil (hydrophobic extract) (CAS 8002-65-1);
  • compound B-5.8 (3-difluoromethyl-l-methyl-lH-pyrazole-4- carboxylic acid (2-bicyclopropyl-2-yl-phenyl)-amide) is described in WO 03/74491;
  • compound B-5.9 (3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (9-isopropyp-l,2,3,4- tetrahydro-l,4-methano-naphthalen-5-yl)-amide) is described in WO 04/35589 and in WO 06/37632;
  • compound B-5.10 (l,3-dimethyl-5-fluoro-lH-pyrazole-4-carboxylic acid [2- (l,3-dimethylbutyl)phenyl]-amide) is described in WO 03/10149;
  • compound B-5.11 (3- difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid (3',4')
  • compositions according to the invention may also comprise more than one of the active components (B), if, for example, a broadening of the spectrum of disease control is desired. For instance, it may be advantageous in the agricultural practice to combine two or three components (B) with component TX.
  • An example is a composition comprising a compound of formula (I), azoxystrobin and cyproconazole.
  • the compound of the formula I is preferably a compound of Tables 1-24.
  • the mixing ratios can vary over a large range and are, preferably 100: 1 to 1:6000, especially 50: 1 to 1:50, more especially 20: 1 to 1:20, even more especially 10: 1 to 1: 10.
  • Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
  • mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient” relates to the respective mixture of TX with the mixing partner).
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
  • other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • the mixtures comprising a TX selected from Tables 1-24 and one or more active ingredients as described above can be applied, for example, in a single "ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds of formula I selected from Tables 1-24 and the active ingredients as described above is not essential for working the present invention.
  • the following non-limiting Examples illustrate the above-described invention in greater detail without limiting it.
  • the crude material was purified by chromatography on silica gel (eluent: heptane/ ethyl acetate 9: 1 (v:v) with 0.5 %v/v of triethylamine), giving a light orange gum.
  • the material was dried in high vacuum to give an orange gum (104 mg).
  • reaction mixture was allowed to warm to room temperature and further stirred at that temperature for 5 hours, giving a yellow solution.
  • the reaction was then cooled using an ice bath and aqueous sodium hydroxide solution (8N; 35 mL) was added to the reaction mixture over 20 minutes to give an orange suspension, which was stirred at room temperature for a further 4 hours.
  • This gum was further purified by flash chromatography over silica (eluent: heptanes: ethyl acetate 2: 1). This gave a yellow gum (0.09g; 52% pure). This was used without further purification. This was used without further purification.
  • the reactor was charged with a solution of (4-methyl-quinolin-2-yl)-methanol (9g; 52 mmol) in trifluoroacetic acid (90 ml.) and a suspension of platinum (IV) oxide hydrate in trifluoroacetic acid. After 2h at 22°C/4 bar/H 2 uptake 99%, a NMR control (1H NMR, CDCI3 after a basic work-up of the sample with aq. NH 3 ) indicated complete and clean conversion.
  • the catalyst was filtered off, and the solvent was removed in vacuo to give a dark brown oil.
  • the reactor was charged with a solution of 4-ethoxy-quinoline (1.86g) in trifluoroacetic acid (17 ml.) and a suspension of platinum(IV) oxide hydrate (1.08g) in trifluoroacetic acid.
  • NMR control (* ⁇ NMR, CDCI 3 after a basic work-up of the sample with aq. NH 3 ) indicated complete and clean conversion.
  • Step B preparation of 4-Difluoromethyl-2-methyl-5,6,7,8-tetrahydro-quinoline :

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Abstract

La présente invention porte sur des composés de formule (I), dans laquelle G1, G2, G3, G4, G5, G6, Y1, Y2, Y3, Y4, Y5 et Y6 et p et q sont tels que définis dans les revendications. L'invention porte en outre sur des compositions qui comprennent ces composés, et sur leur utilisation en agriculture ou en horticulture pour lutter contre ou prévenir une infestation de plantes par des micro-organismes phytopathogènes, de préférence des champignons.
PCT/EP2011/063018 2010-07-29 2011-07-28 Nouveaux dérivés éthers de dioxime microbicides WO2012013754A1 (fr)

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US13/813,131 US20140162980A1 (en) 2010-07-29 2011-07-28 Novel microbiocidal dioxime ether derivatives
CA2804355A CA2804355A1 (fr) 2010-07-29 2011-07-28 Nouveaux derives ethers de dioxime microbicides
CN201180037088.9A CN103038217A (zh) 2010-07-29 2011-07-28 新颖的杀微生物的二肟醚衍生物
BR112013002073A BR112013002073A2 (pt) 2010-07-29 2011-07-28 derivados de éter de dioxima microbicidas
EP11736114.7A EP2598487A1 (fr) 2010-07-29 2011-07-28 Nouveaux dérivés éthers de dioxime microbicides
AU2011284714A AU2011284714A1 (en) 2010-07-29 2011-07-28 Novel microbiocidal dioxime ether derivatives

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CN106478494B (zh) * 2016-09-22 2019-03-15 南通海迪新材料有限公司 2,3,5,6-四氯-4-甲磺酰基吡啶的生产方法

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2641901A1 (fr) * 2012-03-22 2013-09-25 Syngenta Participations AG. Nouveaux microbicides bisoximes
WO2013139822A1 (fr) * 2012-03-22 2013-09-26 Syngenta Participations Ag Nouveaux microbiocides bisoxime

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AU2011284714A1 (en) 2013-01-31
AR082405A1 (es) 2012-12-05
CA2804355A1 (fr) 2012-02-02
BR112013002073A2 (pt) 2016-05-24
US20140162980A1 (en) 2014-06-12
CN103038217A (zh) 2013-04-10
EP2598487A1 (fr) 2013-06-05
UY33538A (es) 2012-02-29

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